Mail issue with MS exchange server on macOS Catalina

I have the same issue.

How long did things work for you with a new account?

How has this not been solved yet? Exchange 2016 servers are incredibly common...

Well, I think you might be right - it is back again. I will post more in a few minutes.

MacMichael64 wrote:

@John P.

I tried this several times and I am talking about issues with MS Exchange server not about Exchange (Office 365).

A not efficient workaround is, to delete the exchange account on the MAC completely, then create it new. This works then for several days, than this workaround has to be repeated. With a large E-Mail-Database this takes quite a long time, and some E-Mail attachements are most of the times lost afterwards.

Acknowledged. When you say large e-mail database, exactly how much mail do you have in your Exchange account? --Have you tried IMAP as a test or workaround?

The reason I ask is this may be relevant...

"If certificate authentication is enabled on the mail server, make sure that your mailbox has no more than 11,000 messages. Microsoft recommends no more than 5000 messages per Exchange mailbox."

https://support.apple.com/en-us/HT201951

@Armando that's the point I wanted to make: you have a VPN client on your system you're not always using. Who else has mail issues on exchange and has a VPN client? (that's not always being used).

Keep you posted on further investigations on network side and connection made by the client.

(it's about routing traffic)

I also have had this issue.

Even with 10.15.4, end of May 2020

It definitely only occurs with my exchange server and Apple-Mail.

Deleting the account and Add it again will help - for some hours, sometimes for some days

I have been suffering, with all of you, the problems of Catalina Apple Mail and Exchange.  I have included my reports to Apple via Feedback in the “additional text.”

I am writing today to report a potential solution.

On Thursday, I rejoined Apple's JointVenture support plan.  I had purchased this previously but let its subscription lapse.  For this single primary email problems reported here (my 1/28/2020 report in this thread), I rejoined at a cost of $500.  I scheduled a service call for Friday afternoon.  I was connected with a senior support person known to me only as Rebecca.  She was knowledgable and did not talk down to me.  It was actually quite pleasant.  She proposed the solution described below.

As an aside, there was one additional problem I did not report: Apple Mail did not adhere to the "check for new messages" preferences setting.  Regardless of whether I set to check the servers ever 1 minute or 5, once or twice an hour, Mail would connect to the server in much shorter intervals: as reported by one of my POP services, 1 connection every 0.1240 minutes (7.44 seconds)!!  At about the same time, my service had updated their software so I wasn't sure who the offender was/. I finally sniffed the network and found that Mail was indeed coming in at sub-minute times between checking.

So, where am I going with all this?

All of the problems I experienced and reported in this thread have been fixed, including that one I did not report.  At Rebecca's suggestion, I created a new user on my system and, once logged in, created a new Mail Exchange email account.  I did the same for MS Outlook.  As I had before, I ran them side by side.  As I read an email in Apple Mail, within a few seconds, the email entry in Outlook changed from unread to read.  When I deleted a message or moved it to another folder (on my system), the message disappeared from the list on Outlook.  Outlook even reflected the flagging (though I didn't check for proper colors).

The rest of my 570k email messages spread in various mailboxes were exported from Mail in my old login and transferred to and imported to Apple Mail in my new account.  As I keep all of my files (including photos and music) in a separate directory in /Users, the rest of the migration wasn't that painful.  I avoided the migration utility or wholesale copying of stuff to avoid unnecessary and potentially troublesome state from coming over.  I can detail more how I run my systems if anybody is interested.

My login on my Catalina has evolved through manual copying and eventually Migration Assistant from my earliest days on a Mac (I converted from UNIX to Macs in 1991).  I could see older pref files and who knows what else.  So, this maybe was a good thing to do - a little rebellion now and then is a good thing.  As a side benefit, the fan on my Mac runs MUCH less than it had - subjective but noticeable.

I have been testing this solution as I enabled more and more of my environment (licenses, passwords, etc. for other applications) and little widgets (MenuMeters, JAC, Grabbit, FSMonitor, Microsoft Office products, etc.).  So, for the most part, I'm pretty much up and running.  But, the real test will come over the next several days during high activity on the Work Exchange server and me being tied to doing real work (MS Teams, etc.).

Other potential suggested fixes here have lasted a few days, if at all.  So, if, by the end of this week, things are still working fine, I will declare victory and recommend more of you create a new account and start from fresh.

Sorry to be so verbose but this has been a significant pain for too long a time.  My one regret is that there isn't enough information available in the system (or, seemingly, experience outside of Apple Engineering) to really debug and find the problem.  But, if we are through this gauntlet, wonderful.

For what its worth, I will report back here near the end of the week (or sooner if the situation regresses).

   aps

Configuration:

MacBook Pro (16-inch, 2019)

MacBookPro16,1

Memory: 16 GB 2667 MHz DDR4

Graphics: AMD Radeon Pro 5500M 4 GB

Intel UHD Graphics 630 1536 MB

Storage: 2 TB flash

Displays: Dual (side-by-side) 27" Thunderbolt Displays

Thunderbolt to USB-C adaptor

This system was purchased in March; the same was occurring on my previous MBP, a Mid-2017 MacBookPro14,3.

Hi Everyone, That is the original issue, once you delete your email account and recreate it in Apple mail, it all works again. What I was asking for is a technical reason as to why it stops receiving email in the first place and perhaps a fix. Or an acknowledgement by Apple tech support that this is a known issue and they are working on it. YES IT WILL WORK AFTER A RECREATION OF YOUR ACCOUNT MAYBE FOR 3 MONTHS IF YOU ARE LUCKY BUT IT WILL HAPPEN AGAIN. That is not fix.

I hope this helps a few of you.

Here is what I found out with 2 of my macs, OS catalina.

No matter how many times, I cleaned up and started with a new profile, this issue always came back.

After reading someone's input here, who mentioned about VPN and any sort of software used to tunnel into enterprise networks, I gave it a short, closing my VPN apps, and using my exchange without VPN connections.

My email is on the cloud - office 365 (just to be clear) adding it via exchange and manually connecting to it without a VPN client - in apple mail seems like I see a difference. I did give up on Apple, after entering a ticket and still getting no where, they pointed to Microsoft being the problem, and I don't care whether apple mail is a path through or not, it worked just fine before they fooled around with this OS, I think they owe it to all the appleheads to figure out what is broken where without taking a penny more from its consumers.

We are a few updates in with catalina and still no bloody fix!

Hi Mamabearfam.

I agree that something changed when, I think, Catalina but I no longer remember.

More detail with some history..

As I initially reported here on Jan 28, 2020, I was also experiencing this problem with my Apple Mail client: I could download and read emails from Exchange (Outlook) but the Exchange server (through the Mac Outlook client or logging in to Office365) did not seem to show any status updates as I read, responded to, or deleted emails.

After a suggestion offered Joint Venture Support Specialist during a Joint Venture support call (6/19) specifically on this issue. The suggestion was to create a new user and migrate everything over - except email client state. There, I had to basically create everything from scratch.

The next day, I created a new user on my system and, once logged in, created a the Mail Exchange email account entry with my work Exchange credentials. It all appeared to work and work as expected.

It continued to work for about 83 days, just under 3 months, until this last night - but, sometime Friday morning, no longer!!!!

However, something interesting to note.

Others have noticed that things seem to work for a while but then go south. But, I might now have some new information!

My main system is a Mac running macOS Catalina 10.15.6. It is in my home office on one of this "book holders" connected to a pair fo Thunderbolt monitors, sort of permanently (at least during the pandemic). I have another MacBook Pro, that is actually my backup system that is running betas if macOS Big Sur 11 Beta (now at 20A5364e). As it is my backup system, I also have Apple's Mail client set up there for all my accounts, including the Exchange account. (Mail only check manually and the POP accounts are configured to not remove email from the servers.)

I had been using the back up Mac last night in my living room while watching TV, including accessing Exchange mail through the Apple Mail client. (I had quit Mail on the main Catalina.) All was fine on it.

When Exchange stopped displaying updated status from my Catalina Mac's Mail client, I checked the Apple Mail on the Big Sur Mac, expecting it to be just fine. IT WAS NOT!!!! It had the same symptoms.

I created a new user on the Big Sur Mac and set up an Exchange account in the Apple Mail client. That worked out just fine.

So, I went back to my main Catalina, removed the Exchange account from Mail, let it finish cleaning out the associated mailboxes and then quit the Mail client. I later restarted Mail and added an Exchange account with my credentials and it was working again.

I'll report on how this goes...

After having observed this behavior of two clients on two different machines fail at the same time pointing to the same server (farm), I am now a little confused. Perhaps something goes stale or has to be renewed; some credential times out or something; a subtle corruption someplace in the Mac - but not two different ones. Some credential timing out - client side, server side? I no longer am convinced the issue is a client-side issue.

Another thing that is frustrating is how Apple has started to use these directory and file name structures that are just unusable by human beings. With mbox organization, one could go and fix things. The whole mail infrastructure is relatively fragile. Also, I can't partially add credentials to the mail system. So, if I have something wrong or an admin made a mistake, I have to start from scratch with each attempt. Why would somebody design such a thing?? You can leave an account offline.

And, while I'm at it (it's late here in Seattle), I am also equally frustrated by console. I am going to have to dig into learn how to read logs. Also, there seem to be several hundred entries per second. I must have some logging level incorrectly set.

Oh well. Good night.

armando

I discovered what was causing me the issue(s) with Exchange. I hope this is of some use to everyone. 😊

Do not change the personal name (i.e., First & Last Name) in Mail.app but leave it as default (e.g., Jon Doe) or the same as what is in Exchange; otherwise, it gets glitchy with drafts and sending e-mail.

I left all of my Exchange accounts (3x) on their default names and haven't had an issue since with Mail.app in Catalina. (knock on wood)

John

Everything works after I create a new account, delete the old exchange account then a few weeks after it stops syncing correctly again. So I'm using outlook which I hate but don't want to reshuffle my email, then Apple Mail bc it is better at searching and indexing mail lol . I wish Apple Mail would just sync correctly with Exchange all the time :-(